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Outsmart
New York, US · Founded 2024 · 12 known investors
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Outsmart builds an AI-powered learning platform that reimagines higher education. The company serves students and educators by leveraging AI for content generation, gamification, and personalized assessment.
Also known as Outsmart Education
Founders & leadership
Outsmart was founded in 2024 by Regina Ring Gotthilf.
Board
Investors · 12
How we know: Abstract Ventures's portfolio page · open dataset · 5k.vc investor directory · Not right? Tell us
How we know: Forerunner Ventures's portfolio page · Not right? Tell us
How we know: Khosla Ventures's portfolio page · funding news · techcrunch.com · the VCSheet dataset · khoslaventures.com · open dataset · 5k.vc investor directory · Not right? Tell us
How we know: funding news · techcrunch.com · Not right? Tell us
How we know: a partner's Signal profile · funding news · press coverage · open dataset · 5k.vc investor directory · Not right? Tell us
How we know: Tactile Ventures's portfolio page · Not right? Tell us
How we know: funding news · Not right? Tell us
How we know: funding news · techcrunch.com · Not right? Tell us
How we know: a partner's Signal profile · Not right? Tell us
Also in the syndicate · 3
Funding
SEC filings, press & company announcements$36.1M disclosed across 2 of 4 rounds · 2024–2025
- Undisclosed amountseedNov 2024
Khosla Ventures (lead), 20Growth, Karman Ventures, Latitud Ventures, Lightspeed Ventures
Source ↗
▶$23.4MraisedSep 2025 · 7 investors · Other TechnologyRule 506(b)
- Ethan ChoiDirector
- Regina Ring GotthilfExecutive Officer, Director
- Jorge MazalExecutive Officer, Director
- Offering amount
- $25M
- Amount sold
- $23.4M
- First sale
- Sep 2025
- Incorporated
- Corporation, Delaware, 2024
- Federal exemptions
- 06b
▶$12.7MraisedNov 2024 · 4 investors · Other TechnologyRule 506(b)
- Jorge MazalExecutive Officer, Director
- Regina Ring GotthilfExecutive Officer, Director
- Offering amount
- $13M
- Amount sold
- $12.7M
- First sale
- Oct 2024
- Incorporated
- Corporation, Delaware, 2024
- Federal exemptions
- 06b
Source: SEC EDGAR Form D. Amounts as filed; amended filings shown once at their latest values.
Company profile
researched Aug 2026Outsmart, referred to in press coverage as Outsmart Education (a name the founders described as not final), is an early-stage education company founded by three former executives of the language-learning company Duolingo. Its stated mission is to increase access to higher education by improving affordability, access and personalization relative to existing college options. The founding team consists of Jorge Mazal (CEO), formerly Duolingo's chief product officer; Daniel Falabella (CPO), formerly senior director of product for learning at Duolingo; and Gina Gotthilf (CMO), formerly vice president of growth and marketing at Duolingo.
As of November 2024, roughly eight months after its inception in April 2024, the company was operating in stealth mode and had not disclosed its product, pricing or delivery model publicly. Press coverage noted it was therefore unclear whether the company would compete with tuition-comparison tools, low-cost online schooling providers, or college matching platforms. The company said the $13 million seed capital raised would fund hiring and product development.
Founding story
Co-founder and CEO Jorge Mazal has said the concept originated in his own experience financing his education. After moving to the United States for his undergraduate degree without the resources to pay for it, he combined jobs, scholarships and other means to fund his studies, and later completed two master's programs at Harvard and Wharton, accumulating roughly a quarter of a million dollars in debt and taking a part-time job collecting trash at his apartment complex to cover living costs. He described that experience as representative of structural problems in higher education, and developed the idea with fellow former Duolingo executives Daniel Falabella and Gina Gotthilf.
Traction
The principal disclosed milestone is a $13 million seed round announced in November 2024, led by Khosla Ventures with participation from Karman Ventures, Latitud Ventures, Lightspeed Ventures and angel investors including Lenny Ratchinsky and 20Growth. No users, revenue or product metrics have been disclosed.
Latest developments
In November 2024 the company announced its $13 million seed financing and said the capital would be directed toward hiring and further product development, while continuing to withhold details of its offering.
▸Full profile — market position, go-to-market, history, risks & controversies
Market position
The company entered a market that includes tuition-comparison platforms such as Tuition Tracker, providers of lower-cost online schooling, and college matching services such as College Rover and College Simply. Because its offering was undisclosed at the time of its seed announcement, its precise positioning within these categories was not established publicly. Management stated an intention to be better than existing higher-education options on access, affordability and personalization.
Stated intent to improve on incumbent higher-education options across access, affordability and personalization, backed by a founding team with senior product, learning and growth experience from Duolingo.
Go-to-market
Prospective and current college students, particularly those for whom the cost of tuition and student debt is a barrier to obtaining a higher-education degree.
History
The company was founded in April 2024 and remained in stealth mode through at least November 2024, when it announced a $13 million seed round led by Khosla Ventures. Its three co-founders worked together at Duolingo for five years; prior roles across the team include Dropbox and Lucid Software (Falabella), Tumblr (Gotthilf), and Lucid, MyFitnessPal and Zynga (Mazal).
Risks & controversies
Product plans, business model and go-to-market approach were undisclosed as of the November 2024 seed announcement, leaving it unclear how the company would fit into or compete with existing college-access, tuition-comparison and online-education categories. The company also operates against a backdrop of rising tuition, with average tuition and fees at private ranked colleges up about 5.5% year over year for the 2024-2025 school year and roughly $1.6 trillion in outstanding US student loan debt.
Compiled by commissioned research from 3 cited public sources — announcements, filings, and press listed under research sources below.
Key figures
latest reportedCompany-reported or press-reported figures, each dated to when it was claimed — not independently audited.
Timeline · 1
launches, deals, and filingsThe company, founded by three former Duolingo executives, announced a $13 million seed round led by Khosla Ventures with participation from Karman Ventures, Latitud Ventures, Lightspeed Ventures and angel investors including Lenny Ratchinsky and 20Growth. Proceeds were earmarked for hiring and product development.
$13M source ↗
Dated company events from announcements, filings, and press; legal rows summarize public dockets and regulator releases.
▸Research sources · 3
primary sources listed
- Ex-Duolingo execs raise $13M for a startup that's making it easier to access a college education | TechCrunchtechcrunch.com · web
3 public sources were cited for this profile; the first-party ones are listed here.
Frequently asked questions
- What does Outsmart do?
- Stealth-stage startup from three ex-Duolingo executives building more affordable, accessible pathways to college education.
- Who founded Outsmart?
- Outsmart was founded by Regina Ring Gotthilf in 2024.
- Who are Outsmart's investors?
- Outsmart's investors include Abstract Ventures, Forerunner Ventures, Khosla Ventures, Latitud Ventures, Lightspeed Venture Partners, Tactile Ventures, 20VC, Karman Ventures and 1 more.
- How much funding has Outsmart raised?
- Outsmart has disclosed $36.1M raised across 2 of its 4 known rounds.
- Where is Outsmart headquartered?
- Outsmart is headquartered in New York, US.